22115-36-2

Usage

Chemical class

Benzopyranones These are organic compounds with a benzene ring fused to a pyran ring.

Bromine atom at the 4th position

This substitution can affect the compound's reactivity and properties.

Phenyl group at the 3rd position

The presence of a phenyl group can influence the compound's steric and electronic properties.

Organic synthesis

The compound can be used as a building block in the synthesis of more complex organic molecules.

Medicinal chemistry

It has potential applications in the development of pharmaceutical drugs due to its unique structure and properties.

Bromine atom

The bromine atom may impart specific reactivity to the compound, making it suitable for various reactions and modifications.

Benzopyranone core

The core structure allows for further functionalization and the synthesis of biologically active molecules.

Building block

The compound serves as an important building block in the synthesis of biologically active molecules due to its unique structure and properties.

Versatility

Its chemical structure and properties make it suitable for a wide range of reactions and modifications, expanding its potential applications in various fields.

Upstream product

• 19096-28-7 3-bromo-2-phenyl-1H-inden-1-one 
• 33578-05-1 methyl 2-(phenylethynyl)benzoate 
• 88180-65-8 isopropyl 2-(2-phenylethynyl)benzoate 
• 83-12-5 phenindione 
• 95-54-5 1,2-diamino-benzene 
• 1084-95-3 2-(2'-phenylethynyl)benzoic acid 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 536-74-3 phenylacetylene 

Downstream Products

• 4809-08-9 3-phenyl-isocoumarin 

Relevant academic research and scientific papers

Synthesis of 3-(Bromomethylene)isobenzofuran-1(3H)-ones through regioselective 5-exo-dig bromocyclization of 2-alkynylbenzoic acids

A direct synthesis of 3-(bromomethylene)isobenzofuran-1(3H)-ones from 2-alkynylbenzoic acids is developed through a regioselective 5-exo-dig bromocyclization. The reaction proceeds smoothly with a broad substrate scope. The products can be further elaborated via a palladium-catalyze cross-coupling reaction, or can convert to other heterocycles through simple operation. Preliminary mechanistic studies reveal that this transformation undergoes a radical process.

Regioselective Synthesis of 4-Aryl-1,3-dihydroxy-2-naphthoates through 1,2-Aryl-Migrative Ring Rearrangement Reaction and their Photoluminescence Properties

4-Aryl-1,3-dihydroxy-2-naphthoates having the less accessible 1,2,3,4-tetrasubstituted naphthalene scaffold and that show photoluminescence emission from solid state as well as in solutions, were selectively synthesized from brominated lactol silyl ethers

Metal-Free Synthesis of 4-Chloroisocoumarins by TMSCl-Catalyzed NCS-Induced Chlorinative Annulation of 2-Alkynylaryloate Esters

4-Chloroisocoumarins can be conveniently prepared from 2-alkynylaryloate esters via the activation of alkynes by electrophilic chlorine, generated in situ from N-chlorosuccinimide (NCS) in the presence of 10 mol % trimethylsilyl chloride (TMSCl), which leads to 6-endo-dig-selective chlorinative annulation to give the desired products in moderate to quantitative yields. The procedure employs readily available reagents and can be conveniently carried out on a wide scope of substrates under mild conditions (0 °C to rt). Furthermore, the reaction is scalable for gram-scale preparation of 4-chloroisocoumarins. Additionally, 4-bromo- and 4-iodoisocoumarins can be prepared in moderate to good yields by replacing NCS with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS), respectively.

Generation of 4-iodoisocoumarins through a TBAI-mediated oxidative cyclization of 2-alkynoates

A tetra-butylammonium iodide (TBAI)-mediated oxidative iodocyclization of 2-alkynoates for the synthesis of various 4-iodoisocoumarin is described herein, and the reaction is highly efficient and shows broad functional group tolerance. This newly develope

NBS-Mediated Oxygen Transfer Reaction of Carbonyl in Ester: Efficient Synthesis of Benzil–o-carboxylate Derivative From o-Alkynylbenzoate

A neighbouring ester group-participated diketonization of o-alkynylbenzoate is described here for the synthesis of benzil-o-carboxylate. Application of the resulting benzil-o-carboxylate in the synthesis of quinoxalines is also reached from o-alkynylbenzoate in an one-pot fashion. This diketonization proceeds smoothly with a high regioselectivity under mild conditions. Importantly, neighbouring group plays an important role in diketonization. A plausible mechanism suggests that a bromo-incoporated isocoumarin cation is described as an intermediate, and the whole process is constituted by NBS-mediated electrophilic 6-endo annulation and oxygen transfer reaction through NBS-mediated oxidative ring-opening. Water serves as a nucleophile of ring-opening. (Figure presented.).

Synthesis of benzil-o-carboxylate derivatives and isocoumarins through neighboring ester-participating bromocyclizations of o-alkynylbenzoates

Bromide mediated neighboring ester-participating bromocyclizations of o-alkynylbenzoates are described here for the synthesis of benzil-o-carboxylates. 4-bromoisocoumarins are also synthesized when phenyl o-alkynylbenzoate is used as the substrate. Mechanistic studies suggest that the whole process is composed of an electrophilic bromocyclization and a dibromohydration-based ring-opening, and the neighboring ester group participates in the bromocyclization. Interestingly, the two oxygen atoms of the keto carbonyls in benzil-o-carboxylates are both derived from water. The electrophilic bromo source is in situ generated from the oxidation of bromide.

One-pot synthesis of 2-(quinoxalin-2-yl)benzoate through NBS-mediated sequential reaction of 2-alkynylbenozate and aryl-1,2-diamine

A metal-free route involving a sequential reaction of 2-alknylbenzoate and aryl-1,2-diamine is described for the generation of 2-(quinoxalin-2-yl)benzoate. The sequential reaction combines NBS-mediated diketonization of 2-alknylbenzoate and condensation reaction with aryl-1,2-diamine, and proceeds smoothly under mild reaction conditions and an array of 2-(quinoxalin-2-yl)benzoate is achieved with high efficiency and excellent functional group tolerance. Mechanism studies indicate oxygen transfer reaction is observed and water is incorporated into neighboring ester group.

Halocyclization of methyl 2-alkynylbenzoates to isocoumarins using cupric halides

Treatment of methyl 2-alkynylbenzoates with two to three equivalents of CuX2 (X = Cl or Br) in refluxing acetonitrile gave isocoumarins 2 in good to excellent chemical yields.

Cy2NH·HX-promoted cyclizations of o-(alk-1-ynyl)benzoates and (Z)-alk-2-en-4-ynoate with copper halides to synthesize isocoumarins and α-pyrone

Cy2NH·HX was found to improve the cyclization reactions of o-(alk-1-ynyl)benzoates and (Z)-alk-2-en-4-ynoate with CuX2 (X = Cl, Br) to synthesize the corresponding 4-haloisocoumarins and 5-bromo-2-pyrone, respectively. In the presenc

Organomercury Mediated Synthesis of Isocoumarins

A facile and convenient synthesis of isocoumarins via an organomercurial route is reported.The synthesis involves reaction of methyl 2-alkynbenzoates with mercuric acetate to give the corresponding isocoumarin mercurials which serve as intermediates to afford the appropriate isocoumarins having substituents as Cl,I,Br,COCH3 etc.